Title of article
Highly chemoselective Pummerer reactions of sulfinyldiacetic acid derivative
Author/Authors
Nagao، نويسنده , , Yoshimitsu and Miyamoto، نويسنده , , Satoshi and Hayashi، نويسنده , , Kazuhiko and Mihira، نويسنده , , Ado and Sano، نويسنده , , Shigeki، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2002
Pages
4
From page
1519
To page
1522
Abstract
Sulfinyldiacetic acid amide ester rac-1 was efficiently synthesized starting from thiodiacetic acid 4. Treatment of rac-1 with Ac2O and TMSOTf in CH2Cl2 at −40°C gave chemoselectively amide site α-acetoxy sulfide rac-2 in a ratio (91:9) of rac-2 and rac-3 and in a 90% total yield. Similar treatment of 1 with Ac2O and TMSOTf in DMF at room temperature furnished ester site α-acetoxy sulfide rac-3 in a highly chemoselective manner (rac-2:rac-3=3:97) and in a 92% total yield.
Keywords
Lewis acid , solvents and solvent effects , sulfoxides , Chemoselectivity , Pummerer reactions
Journal title
Tetrahedron Letters
Serial Year
2002
Journal title
Tetrahedron Letters
Record number
1650105
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